NP-MRD: Showing NP-Card for Camarinic acid (NP0070987)

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Record Information

Version

2.0

Created at

2022-04-28 16:23:22 UTC

Updated at

2022-04-28 16:23:22 UTC

NP-MRD ID

NP0070987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Camarinic acid

Description

(1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]Tetracos-4-ene-11-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Camarinic acid is found in Lantana camara, Lantana camara LINN. and Tilesia baccata. Based on a literature review very few articles have been published on (1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]Tetracos-4-ene-11-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218232D          

 38 43  0  0  1  0            999 V2000
    7.2178    0.7230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.3986    0.6254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9045    1.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  8 13  1  0  0  0  0
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  1 38  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282218232D          

 38 43  0  0  1  0            999 V2000
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    2.2045    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5472   -0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3525   -1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8026    0.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3684   -0.0072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -1.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367   -2.2124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7819   -1.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8810   -1.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7002   -1.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0253   -0.5007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1943   -1.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5429    1.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 13 16  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 28  1  0  0  0  0
 23 29  1  1  0  0  0
 12 30  1  1  0  0  0
  4 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  3 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  1 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](OC(C)=O)[C@@]2(CC[C@]3(C)C(=CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@]5(O)CC[C@]43CO5)[C@@H]2[C@H]1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-18-16-24(38-20(3)33)31(26(34)35)14-12-28(6)21(25(31)19(18)2)8-9-23-29(28,7)11-10-22-27(4,5)32(36)15-13-30(22,23)17-37-32/h8,18-19,22-25,36H,9-17H2,1-7H3,(H,34,35)/t18-,19+,22+,23+,24-,25+,28-,29-,30-,31-,32+/m1/s1

> <INCHI_KEY>
BVPSHWDVSJULFR-XEXVZANXSA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
59.9975978410546

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]tetracos-4-ene-11-carboxylic acid

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
5.254666660999998

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.685010456202475

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.399366313454861

> <JCHEM_PKA_STRONGEST_BASIC>
-4.248776436297578

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
144.20729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.49e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]tetracos-4-ene-11-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.473   1.350   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.396   0.116   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.789  -1.299   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.260  -1.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.337  -0.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.944   1.167   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.022   2.401   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.808  -0.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.886   0.803   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.357   0.621   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.750  -0.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.672  -2.028   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.201  -1.846   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.124  -3.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.653  -2.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.594  -3.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.747  -3.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.180  -3.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.463  -1.758   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.170  -0.274   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.115   1.197   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.618   1.633   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.222   0.123   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.888  -1.316   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.469  -1.913   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.525  -2.812   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.807   0.169   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.231   1.151   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.688  -0.013   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.005  -3.531   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.182  -2.714   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.575  -4.130   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.526  -3.466   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.711  -2.532   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      16.240  -2.350   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.847  -0.935   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      17.163  -3.583   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.080   2.765   0.000  0.00  0.00           C+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   15   31                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17   30                                             
CONECT   13   12    8   14   16                                             
CONECT   14   13   15                                                       
CONECT   15   14    4                                                       
CONECT   16   13                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   11   21   28                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27   29                                             
CONECT   24   23   19   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27   20                                                       
CONECT   29   23                                                            
CONECT   30   12                                                            
CONECT   31    4   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    3   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(Acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0,.0,.0,.0,]tetracos-4-ene-11-carboxylate	Generator

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

(1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]tetracos-4-ene-11-carboxylic acid

Traditional Name

(1S,2S,6S,7S,8R,10R,11S,14S,15R,18R,20S)-10-(acetyloxy)-20-hydroxy-7,8,14,15,19,19-hexamethyl-21-oxahexacyclo[18.2.2.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]tetracos-4-ene-11-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](OC(C)=O)[C@@]2(CC[C@]3(C)C(=CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@]5(O)CC[C@]43CO5)[C@@H]2[C@H]1C)C(O)=O

InChI Identifier

InChI=1S/C32H48O6/c1-18-16-24(38-20(3)33)31(26(34)35)14-12-28(6)21(25(31)19(18)2)8-9-23-29(28,7)11-10-22-27(4,5)32(36)15-13-30(22,23)17-37-32/h8,18-19,22-25,36H,9-17H2,1-7H3,(H,34,35)/t18-,19+,22+,23+,24-,25+,28-,29-,30-,31-,32+/m1/s1

InChI Key

BVPSHWDVSJULFR-XEXVZANXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lantana camara	LOTUS Database	35616633
Lantana camara LINN.	Plant	KNApSAcK
Tilesia baccata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Naphthopyran
Naphthalene
Dicarboxylic acid or derivatives
Oxane
Pyran
Cyclic alcohol
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.11	ALOGPS
logP	5.25	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	144.21 m³·mol⁻¹	ChemAxon
Polarizability	60 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163003492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Camarinic acid (NP0070987)

MOL for NP0070987 (Camarinic acid)

3D MOL for NP0070987 (Camarinic acid)

3D SDF for NP0070987 (Camarinic acid)

3D-SDF for NP0070987 (Camarinic acid)

PDB for NP0070987 (Camarinic acid)

3D PDB for NP0070987 (Camarinic acid)

SMILES for NP0070987 (Camarinic acid)

INCHI for NP0070987 (Camarinic acid)

Structure for NP0070987 (Camarinic acid)

3D Structure for NP0070987 (Camarinic acid)